Hydrochloric Acid → HCID 18974745, compound

HRID 2393239Notes

Reaction equation

HRID 2393239 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.O1CCCC1.[Cl:16][C:17]1[CH:22]=[C:21]([O:23][C:24]2[N:29]=[C:28]([C:30](OC)=[O:31])[CH:27]=[CH:26][CH:25]=2)[CH:20]=[CH:19][N:18]=1.Cl>C(OCC)C.CCCCCC.C(OCC)(=O)C>[Cl:16][C:17]1[CH:22]=[C:21]([O:23][C:24]2[N:29]=[C:28]([CH2:30][OH:31])[CH:27]=[CH:26][CH:25]=2)[CH:20]=[CH:19][N:18]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 18974747HCID 18974747, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 18974745HCID 18974745, compoundYield 62.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
-50 °C

Procedure

A one molar solution of diisobutylaluminum hydride in tetrahydrofuran (200 mL, 0.2 mol) is added over 45 minutes to a solution of methyl 6-[(2-chloro-4-pyridyl)-oxy]picolinate (18.15 g, 0.069 mol) in diethyl ether (300 mL) at -50° C. Under a nitrogen atmosphere. The reaction mixture is stirred at -50° C. for two hours, allowed to warm to 0° C., and acidified with dilute hydrochloric acid. The phases are separated and the aqueous phase is extracted with diethyl ether. The organic extracts are combined with the organic phase and the resultant solution is washed with saturated sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain an oil. Flash column chromatography of the oil using silica gel and a 7:3 hexane/ethyl acetate solution gives the title product as a colorless oil (10.2 g, 62.5%).

Workup

  1. temperatureto warm to 0° C.
  2. customThe phases are separated
  3. extractionthe aqueous phase is extracted with diethyl ether
  4. washthe resultant solution is washed with saturated sodium hydrogen carbonate solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customto obtain an oil

Sources & evidence

ORD record
ord-3b152f2792434cea91c5a9ca225d0e2e
Source dataset
uspto-grants-1998_09
Patent number
US05807804

Reaction notes

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